With a bevy of daring ensembles and bold beauty looks to her credit, Meester makes her mark.

Not to be outdone by her popular alter-ego Blair Waldorf, Meester has proved she's much more than a preppy gossip girl. Whether she's climbing the pop music charts or stealing the silver screen in Country Strong and The Roommate, Meester's fashion and beauty looks are similarly out of character. Here, her vast and varied sartorial choices.

September 2006: Fashion You can't be born a Blair Waldorf; you have to grow into one. Meester hadn't made her debut as queen of the Upper East Side and was clearly still prisoner of unflattering tube dresses from the high school prom scene. But her bright-blue sheath and electric-purple sandals prove that even then she knew how to stand out in a crowd!